With some experience under my belt, my second happy ending massages goes much smoother.
Last time I posted about the set of 'firsts' I had at a happy ending massage. After that story took place, I moved to the city to finish my study. I thought that meant I would have some time to enjoy more massages but it turns out I was too busy for that.
During that time I did some dating and made out with a woman I met at uni, but things didn't work out (through no fault of our own). After that year, I got an office job and started to have some free time and money again.
I was living in a suburb very close to the city, near lots of brothels and after doing some research, I found one that had a massage option. I was still a virgin and still adamant on not losing it to a prostitute. Things lined up on the Thursday night before a long weekend.
Ahead of the long weekend, we had drinks at the office, where I enjoyed a glass or two of wine. After that I rushed home, got changed (in case someone saw me) then headed back out. This brothel was like a lot of the others in the area as it focused on Asian women.
I went in and met the line-up of women. I picked a tall, slender woman (who also looked slutty, like a pornstar) but the receptionist said she wouldn't be interested in just a massage service, so I picked another woman I liked - east Asian with pale skin, short, button cute face and friendly.
I went up to the room and showered, lay on the bed, then she came to join me. She stripped her top off and was in just a garter. She asked if I wanted oil and then started to 'massage' me. However I could tell this wasn't like the last place I visited that specialised in erotic massage, as her massage was mostly some light, almost annoying pinches up and down the backs of my legs and occasionally over my back. But I didn't have long to worry, after a moment or two of that she started to stroke her finger up and down the crack of my ass and over my balls.
If you remember from my story last time, I had a little trouble getting hard. I'm not sure if it was the confidence following my previous experience, some relaxation from the wine (I wasn't even really tipsy) or her touch but that soon had me growing rock hard.
She told me to roll out so I proudly rolled out, my cock fully hard and straining into the air. "Wow! Grrrreat cock" she said as she wrapped her hand around it and bent it back further from my body, tilting the head around a little to give it a good look (I'm almost 8 inches long and curved up). She starts to stroke me eagerly "You want me to suck?" she asked, but I knew that would cost extra and would need a condom. "You want jiggy jig?" I took a moment for me to process, so she made the pumping motion with her arms and hips. I politely refused both offers.
Knowing she's in for a handjob she told me courteously "If you want anything just tell me ok, if you want faster or slower" by then her hand was pumping it pretty quick and I wanted to last longer so I told her to slow down a bit. She'd slow down a bit but kept getting faster a few times after I told her to slow it down, so I decided to relax and let her do it her way as I wrapped my arm around her to stroke up and down her back. My cock felt like it was the hardest it had ever been and her oily hand felt so good sliding up and down it.
As she stroked me, I reached around to stroke around the curves of her breasts, they might have been C cups and were fairly big for an Asian women with her build. I looked at her nipples as my fingers grazed over them, then I reached down to touch her pussy but she said it would cost extra to do that so I just enjoyed stroking her breasts and thighs.
After a few minutes of her pumping away at my rock hard cock I could feel the urge coming on and told her I was going to cum, I pumped my hips up to her hand as she jerked it and made me cum on my stomach.
She cleaned me up, then lay next to me, making casual chat as I caught my breath. I booked for 45 minutes so that I wouldn't be rushed and from what I had read, most times you only get to cum once and are charged extra to cum a second time, so I thought that was the end for me and maybe I could give her a massage in return. But before I could offer, she reached down and grabbed my still engorged but soft cock at the base and flopped it to the side making a funny noise like 'ehh'. I laughed as I said it's still recovering, but a few moments later she reached down and started stroking it gently until I grew hard again.
I was pretty pleased, compared to the nerves of my first time, now I had gotten it up twice in the one booking. She started stroking me again. It was harder to cum this second time and she started saying her arm was sore in a comical way, using her other hand to help the one she had wrapped around my cock, making little grunts like it was hard work. I thought to myself 'that's your fault for getting it up again ha'.
I wasn't sure if I could get there in time before the end of the booking, so I took over for a bit, pumping it furiously as I stared at and played with her tits. We took it in turns. Eventually I got close so I told her and got her hand back on me to finish me off onto my stomach again. I was over the moon as I lay on the bed watching her shower. Then I showered myself, said goodbye and headed off.
Now for the punchline: The brothel is across the road from a mechanics. As I was heading out back onto the street, there was a middle aged man working late at the mechanics, he saw me walking out and called out something I didn't catch followed by "You have no will power!". I laughed to myself "Jokes on you, you don't know I was just naked and hard with a woman asking to fuck and I still didn't do it. Bet I have more willpower than you!"

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